There funding is almost never secured for more then a year at a time.

Giving up $100k+,in tax free income.

Dont see how that could even remotely be possible when U have NO state income tax ..

I would not offer furnished rentals in lower income areas. 

My CPA says that I don't need to report the income any differently than I have been so this is a plus (less hassle). 

I still think they need to upgrade their security for me to trust their system again but at least their customer support was able to sort it out, just took some time.

Securing legitimate deals is a great first step.

Rentals generate passive income, so an S-Corp offers no added tax benefit.

Ensure you collect a proper security deposit (typically one month's rent in Florida) to cover potential damages.Your plan to increase rent next year makes sense given rising costs (taxes, insurance, and maintenance).

Exchange now at 500k over basis into income property with lease back and put option for 300k more.